Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Hydrazine | HCID 9321 | — |
| Reactant | 3-Methylbenzaldehyde | HCID 12105 | — |
| Reactant | HCID 57935895 | HCID 57935895 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 68920264 | HCID 68920264 | 36.9% |
Reaction Steps
To a solution of compound C (33 mg, 0.1 mmol) in 3 mL of dioxane was added an excess amount of hydrazine (0.02 mL, 0.65 mmol). The resulting mixture was heated at 90° C. for 2 h. The reaction mixture was cooled to room temperature and diluted with methylene chloride, followed by washing with brine twice. The organic phase was dried and concentrated. The left residue was dried in vacuo, and then dissolved in 5 mL of methanol. To the above solution was added m-tolualdehyde (0.01 mL, 0.11 mmol) and a catalytic amount of acetic acid. After the reaction mixture was heated at 50° C. for 30 min, the mixture was cooled to room temperature. A small amount of precipitate was observed and collected to give 15 mg of the final product, N-(6,7-Dimethoxy-2-morpholin-4-yl-quinolin-4-yl)-N′-(3-methyl-benzylidene)-hydrazine (compound 7).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08318730B2 |
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| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-449753041f6e4e7c93456c0c5be31b1a |
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| Source note | uspto-grants-2012_11 |
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